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Thermisch und photochemisch induzierte intramolekulare, 1,3-dipolare Cycloadditionen von 5-(2-Allyloxyphenyl)-2-phenyltetrazol


Meier, Hansruedi; Heimgartner, Heinz (1977). Thermisch und photochemisch induzierte intramolekulare, 1,3-dipolare Cycloadditionen von 5-(2-Allyloxyphenyl)-2-phenyltetrazol. Helvetica Chimica Acta, 60(297):3035-3038.

Abstract

The title compound 5 is easily obtained by a recently described procedure (Scheme 2). The tetrazole 5 reacts at 165-170° or on irradiation at room temperature to yield 2-phenyl-3,3a-dihydrochromano[4,3-c]pyrazole (7, Scheme 3), which probably arises by intramolecular [3+2]-cycloaddition of the intermediate nitrilimine. Dehydrogenation of 7 with chloranil leads to 2-phenylchromano[4,3-c]pyrazole (8, Scheme 3).

Abstract

The title compound 5 is easily obtained by a recently described procedure (Scheme 2). The tetrazole 5 reacts at 165-170° or on irradiation at room temperature to yield 2-phenyl-3,3a-dihydrochromano[4,3-c]pyrazole (7, Scheme 3), which probably arises by intramolecular [3+2]-cycloaddition of the intermediate nitrilimine. Dehydrogenation of 7 with chloranil leads to 2-phenylchromano[4,3-c]pyrazole (8, Scheme 3).

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Additional indexing

Other titles:Thermal and Photochemically Induced Intramolecular 1,3-DipoIar Cycloaddition Reactions of 5-(2-Allyloxyphenyl)-2-phenyltetrazole
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1977
Deposited On:29 Oct 2014 10:31
Last Modified:05 Apr 2016 18:26
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
Publisher DOI:https://doi.org/10.1002/hlca.19770600855

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